Homosulfanilamide salts of benzalthiosemicarbazones



.3 This application is a continuation-impart of our copending application Serial No. 106,744, flied July 25, 71949, now Patent No. 2,605,262.

The invention is further illustrated by the following examples, parts indicated being by weight:

Example 1 A solution of about 111.5 parts of benzaldehydethiosemicarbazone-a-carboxylic acid in 500 parts of aqueous ammonium hydroxide (1N) is reacted at 70 C. with a solution of 111.5 parts of the hydrochloric acid salt of 4-aminomethylbenzenesulfonamide in 500 parts of water. The product salt, after being recrystallized, is obtained as light-yellow crystals which slowly decompose when heated to a temperature above 250 C. In an analogous manner, by reacting benzalthiosemicarbaZone-4-acrylic acid with 4-a-aminoethyl-benzenesulfonamide, a salt is obtained in the form of faintly yellow crystals, which char when heated at a temperature above 260 C.

Eample 2 About parts of thiosemicarbazide and 24 parts of ethyl 4-formyl-phenylacetate of the formula:

are refiuxed for one hour in 250 cc. aqueous etha- 'nol (1:1) to which 2 cc. glacial acetic acid had been added. On cooling the solution, the thiosernicarbazone of the formula:

crystallizes in colorless crystals, having a melt- V ing point 0f 151 C.

About 37 parts of this thiosemicarbazone are dissolved in 200 parts of methanol and stirred for one hour at room temperature with 50 parts of a aqueous sodium hydroxide solution,

then the mixture is acidied by addition of hydrochloric acid. A thiosemicarbazone productis obtained as colorless crystals, having a melting point oi 214 C. and being represented by the formula:

About `24 parts of this thiosemicarbazone are A dissolved in 100 parts of aqueous ammonium hy- "droxide solution (1N) and 22 parts of the hydrochloride salt of 4-amnomethylbenzenesulfonamida dissolved in 100 parts of Water is added.

Both solutions, before mixing are heated nearly to the boiling point. Yellow crystals precipitate on cooling, which melt at 218 C. with decomposition. The crystals are a 4-aminornethylbenzenesulfonamide salt of thethiosemicarbazone of theV above formula.

It will be noticed that in each of the preceding R.CH.NH:

wherein R. is a member of the group consisting of hydrogen and methyl and the acid-reacting substituted benzalthiosemicarbazone moiety is represented by the formula:

RII

wherein one member of the group consisting of R and R" is hydrogen and the other is a member oi the group consisting of:

00.011, -CHzCODH and -CH:CH.C0.0H 2. A chemotherapeutically active 4-aminomethylbenzenesulfonamide salt of benzalthiosemicarbaZone-i-carboxylic acid. 3. A chemotherapeutically active 4-aminomethylbenzenesulfonamide salt of benzalthiosemicarbazone--acetic acid. i

4. A chemotherapeutically active 4-a-aminoethylbenzenesulfonamide salt of benzalthiosemicarbazone-i-acrylic acid.

ROBERT BEHNISCH: FRITZ MIETZSCH.

HANS SCHMIDT.

References Cited in the le of this patent4 UNITED STATES PATENTS Number Name Date 2,545,962 Lott et al Mar. 20, 1951 FOREIGN PATENTS v Number Country Date 76,218 Germany Oct. 28, 1943 270,691

Y Switzerland Dec. l, 1950 

1. ALKALINE-REACTING AMINOALKYL-BENZENSULFONAMIDE SALTS OF ACID-REACTING SUBSTITUTED BENZALTHIOSEMICARBAZONES WHEREIN THE AMINOALKYLBENZENESULFONAMIDE MOIETY IS REPRESENTED BY THE FORMULA: 